Category: 622392-04-5

Synthetic Route of 622392-04-5, A common heterocyclic compound, 622392-04-5, name is 2-Bromo-5-iodopyrazine, molecular formula is C4H2BrIN2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a slurry of [1-BENZYL-4- [4- (4,] 4,5, [5-TETRAMETHYL- [1,] 3,2] dioxaborolan-2-yl) – benzenesulfonyl]-piperidine-4-carboxylic acid tert-butyl ester (1) (12.0 g, 22.2 mmol) in toluene (40 mL) was added solid 2-bromo-5-iodo-pyrazine (2) (6.98 g, 24.5 mmol, prepared in accordance with Example 21, Part B), 2 N [NA2C03] (25 mL), ethanol (2.5 mL), and Pd (dppf) Cl2 (0.90 [G,] 1.1 mmol). The resulting mixture was heated at [60C] for 16 hr. Afterward, the mixture was partitioned between EtOAc and water, and then filtered to remove insolubles. The organic layer was separated, washed with brine, dried over [MGS04,] and evaporated to a brown solid. The crude material was purified by flash column chromatography on silica gel (eluting with 5-80% ethyl acetate in hexane) to . afford 6.60 g (52% yield) of the desired product (3) as an off-white solid. LCMS: m/z =572.3, 574.3.

The synthetic route of 622392-04-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMACIA CORPORATION; WO2004/811; (2003); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 622392-04-5, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 622392-04-5, name is 2-Bromo-5-iodopyrazine, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: 3Cz (0.50 g, 1.0 mmol), 5-bromo-2-iodopyridine (0.29 g, 1.0 mmol), copper (0.07 g, 1.0 mmol) and K2C03 (0.28 g, 2.0 mmol) were combined in a 2-necked flask equipped with a condenser and cycled 3 times with vacuum and nitrogen. Chlorobenzene (15 ml_) was then added and stirred at 120 C under the flow of nitrogen for 19 hours whereupon full consumption of both starting materials was observed. The reaction was then allowed to cool and the copper filtered out over Celite bed and washed with DCM. The solvents were removed under vacuum resulting in an off-white solid (0.63 g, 96%).

The chemical industry reduces the impact on the environment during synthesis 2-Bromo-5-iodopyrazine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; UNIVERSITY COURT OF THE UNIVERSITY OF ST ANDREWS; ZYSMAN-COLMAN, Eli; CHEN, Dongyang; PACHAI GOUNDER, Rajamalli; (104 pag.)WO2019/202342; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 622392-04-5, name is 2-Bromo-5-iodopyrazine, A new synthetic method of this compound is introduced below., Recommanded Product: 2-Bromo-5-iodopyrazine

Step 1: N-1-(5-Iodo-pyrazin-2-yl)-2-methyl-propane-1,2-diamine To a solution of 2-bromo-5-iodopyrazine (CAS 622392-04-5) (250 mg, 878 mmol) in 0.7 ml of pyridine, was added 2-methylpropane-1,2-diamine (116 mg, 138 mul, 1.32 mmol, 1.5 equiv.) at room temperature. The colorless solution was stirred for 16 hours at 100 C. The reaction mixture was cooled and concentrated in vacuo. The crude material was used directly in the next step.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Green, Luke; Guba, Wolfgang; Jaeschke, Georg; Jolidon, Synese; Lindemann, Lothar; Ricci, Antonio; Rueher, Daniel; Stadler, Heinz; Vieira, Eric; US2011/251169; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 622392-04-5, name is 2-Bromo-5-iodopyrazine, belongs to Pyrazines compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 622392-04-5, category: Pyrazines

Add 30 g of 2-bromo-5-iodopyrazine, 300 ml of toluene to a 500 ml three-necked flask.Displace nitrogen protection and then add 26.7 ml of hexa-butyltin di-tin.After the reaction solution was stirred at room temperature for 3 hours,0.61 g of tetrakis(triphenylphosphine)palladium was added, and the mixture was heated to 120 C and stirred for 8 hours.The TLC monitors the complete reaction of the starting material to stop the reaction.After the reaction solution is cooled to room temperature, the column removes insoluble impurities.The crude product obtained after concentration of the eluent was recrystallized from toluene to yield 12.6 g of white solid.The yield was 76.2%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-5-iodopyrazine, and friends who are interested can also refer to it.

Reference:
Patent; Xi’an Ruilian New Materials Co., Ltd.; Zhang Hongke; Sun Jun; Liu Kaipeng; Wang Xiaowei; Liu Qianfeng; Gao Renxiao; Cai Liang; Yang Yan; (34 pag.)CN109053696; (2018); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 622392-04-5, A common heterocyclic compound, 622392-04-5, name is 2-Bromo-5-iodopyrazine, molecular formula is C4H2BrIN2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a solution of 2-bromo-5-iodopyrazine (CAS 622392-04-5) (250 mg, 878 muiotaetaomicron) in 0.7 ml of pyridine, was added 2-methylpropane- 1,2-diamine (116 mg, 138 mu, 1.32 mmol, 1.5 equiv.) at room temperature. The colorless solution was stirred for 16 hours at 100C. The reaction mixture was cooled and concentrated in vacuo. The crude material was used directly in the next step.

The synthetic route of 622392-04-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GREEN, Luke; GUBA, Wolfgang; JAESCHKE, Georg; JOLIDON, Synese; LINDEMANN, Lothar; RICCI, Antonio; RUEHER, Daniel; STADLER, Heinz; VIEIRA, Eric; WO2011/128279; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 622392-04-5,Some common heterocyclic compound, 622392-04-5, name is 2-Bromo-5-iodopyrazine, molecular formula is C4H2BrIN2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

2-Bromo-5-iodopyrazine (284.9 mg, 1 mmol), lH-imidazole (64.7 mg, 0.95 mmol), toluene (10 mL), and K2CO3 (345.5 mg, 2.5 mmol), Cul (19.0 mg, 0.1 mmol), trans-N,N’- dimethylcyclohexane-l, 2-diamine (0.032 mL, 0.2 mmol) were heated at 100 C overnight. The reaction mixture was then partitioned between H20 and ethyl acetate. The organic layer was dried over MgSCL, filtered, and concentrated under vacuum. Purification by silica gel chromatography (ethyl acetate in hexane, 0-100%), yielded 2-(lH-imidazol-l-yl)-5-iodopyrazine (219.7 mg, 85%) as an off-white solid which contains a small amount of inseparable byproduct 2-(lH-imidazol-l- yl)-5-bromopyrazine. LC-MS 273.1 [M+H]+, RT 0.74 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-5-iodopyrazine, its application will become more common.

Reference:
Patent; PTC THERAPEUTICS, INC.; CHEN, Guangming; BHATTACHARYYA, Anuradha; JIANG, Yao; KARP, Gary, Mitchell; NARASIMHAN, Jana; TURPOFF, Anthony; ZHANG, Nanjing; (0 pag.)WO2020/5882; (2020); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 622392-04-5, name is 2-Bromo-5-iodopyrazine, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 2-Bromo-5-iodopyrazine

A mixture of 2-bromo-5-iodopyrazine (200mg, 0.704mmol), cesium carbonate (400mg, 1.23mmol) and 2R methyl piperazine (85mg, 0.85mmol) in DMF (1 OmI) was stirred at 1000C overnight. The reaction was cooled and solvent evaporated.Water (100ml) was added and insoluble solid was filtered, then dissolved in MeCb (100ml), dried over Na2SO4, filtered and solvent evaporated yielding product (205mg, 95%)

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 622392-04-5.

Reference:
Patent; SCHERING CORPORATION; WO2008/153858; (2008); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 622392-04-5, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 622392-04-5, name is 2-Bromo-5-iodopyrazine, This compound has unique chemical properties. The synthetic route is as follows.

Description 66: 2-bromo-5-(trifluoromethyl)pyrazine (D66); Potassium fluoride (238 mg, 4.09 mmol) and copper(I) iodide (779 mg, 4.09 mmol) were mixed and heated under vacuum using heat gun (temperature 360 0C, on display of heating gun) for 20 minutes (until a greenish colour of the mixture appeared). After cooling at room temperature, DMF (4 ml) and NMP (4.00 ml) were added followed by (trifluoromethyl)trimethylsilane (0.603 ml, 3.77 mmol) and 2-bromo-5-iodopyrazine D65 (896 mg). The resulting mixture was stirred at room temperature for 5 hours. The reaction mixture was poured in 200 ml of 6N NH3 water solution and was extracted twice with Et2O(3 x 50 ml). Gathered Et2O layers were dried over Na2SO4.Diethyl ether was distilled by Claisen apparatus. It was recovered the title compound D66(586 mg).1H NMR (400 MHz, CHLOROFORM- d) delta ppm 8.73 – 8.81 (m, 1 H) 8.84 (s, 1 H)

The chemical industry reduces the impact on the environment during synthesis 2-Bromo-5-iodopyrazine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; GLAXO GROUP LIMITED; AMANTINI, David; DI FABIO, Romano; WO2010/122151; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 622392-04-5, name is 2-Bromo-5-iodopyrazine, belongs to Pyrazines compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 622392-04-5, Application In Synthesis of 2-Bromo-5-iodopyrazine

A 60% NaH dispersion in mineral oil (0.504 mg, 12.66 mmol, Aldrich) was added to a mixture of 2-cyclopropylethanol (1.0 g, 11.61 mmol, Lancaster) in THF (60 mL). The resulting mixture was stirred at ambient temperature under N2 for 20 min. Subsequently, 2-bromo-5-iodopyrazine (3.0 g, 10.55 mmol, Gateway Chemical) was added, and the resulting mixture was stirred at 65 C. under N2 for 3.5 hr. The mixture was then allowed to cool to ambient temperature overnight. THF was removed in vacuo, and the residue was diluted with ethyl acetate (150 mL) and deionized water (75 mL). The layers were separated, and the aqueous was back-extracted with ethyl acetate (50 mL). The combined ethyl acetate layers were then washed with 75 mL each of sat. NaHCO3(aq) and brine, dried over MgSO4, filtered, and concentrated to an oil in vacuo 3.0 g (~100%). It was observed that the alkoxide did not selectively displace the iodide versus bromide in this reaction. Thus, a mixture of the monoalkoxylated product resulted. This, however, did not matter for the next reaction

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Barta, Thomas E.; Becker, Daniel P.; Bedell, Louis J.; Boehm, Terri L.; Brown, David L.; Carroll, Jeffery N.; Chen, Yiyuan; Fobian, Yvette M.; Freskos, John N.; Gasiecki, Alan F.; Grapperhaus, Margaret L.; Heintz, Robert M.; Hockerman, Susan L.; Kassab, Darren J.; Khanna, Ish K.; Kolodziej, Stephen A.; Massa, Mark A.; McDonald, Joseph J.; Mischke, Brent V.; Mischke, Deborah A.; Mullins, Patrick B.; Nagy, Mark A.; Norton, Monica B.; Rico, Joseph G.; Schmidt, Michelle A.; Stehle, Nathan W.; Talley, John J.; Vernier, William F.; Villamil, Clara I.; Wang, Lijuan J.; Wynn, Thomas A.; US2005/9838; (2005); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 622392-04-5 as follows. Safety of 2-Bromo-5-iodopyrazine

Preparation 11 : iert-Butyl (2S)-2-[5-(5-bromopyrazin-2-yl)-1 H-benzimidazol-2-yl]pyrrolidine-1 – carboxylateTo ieri-butyl (2S)-2-[5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 H-benzimidazol-2-yl]pyrrolidine-1- carboxylate obtained from Preparation 6 (500 mg, 1.21 mmol) and 2-bromo-5-iodopyrazine obtained from Preparation 10 (310 mg, 1 .10 mmol) in toluene (12.5 ml_) and ethanol (1.6 ml_), were added [1 ,1- bis(diphenylphosphino)ferrocene]dichloropalladium(ll) (50 mg, 55 muiotaetaomicronIota) and sodium carbonate (1.1 ml_, 1 M aqueous solution, 1.1 mmol). The reaction mixture was heated at 60 C for 16 hours. After this time, the resulting mixture was cooled to room temperature, diluted with ethyl acetate (30 ml_) and washed with water. The aqueous layer was extracted again with ethyl acetate. The combined organic extracts were dried over MgS04 and the solvent was evaporated under reduced pressure. The crude product obtained was purified by flash chromatography (ethyl acetate : dichloromethane, 1 : 1 ) to give the title compound as a yellow solid (385 mg).LCMS (run time = 5 minutes, System D): Rt = 2.92 minutes; m/z 444 and 446 [MH+]H NMR (400 MHz, CD3OD): delta = 8.40-7.00 (br, 5H), 5.10-5.00 (m, 1 H), 3.75 (m, 1 H), 3.55 (m, 1 H), 2.55-2.35 (m, 1 H), 2.15-1.95 (m, 3H), 1 .10 (s, 9H).

According to the analysis of related databases, 622392-04-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER LIMITED; MILBANK, Jared Bruce John; TRAN, Thien Duc; WAKENHUT, Florian; WO2011/154871; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem